Donald Trump made his splashy debut in the 2016 race by denouncing Mexican immigrants as “rapists.” Now his presidential campaign is distancing the candidate from factually incorrect comments the Trump Organization’s special counsel made about spousal rape in connection with Trump’s own alleged assault on his first wife.

It’s an awkward position for the Trump campaign to be in, but perhaps one that was unavoidable considering the billionaire has given vocal, and at times inconsistent, opinions about sexual assault. Trump has been something of an opportunist when it comes to that subject: he advocated for the death penalty for the alleged attackers in the Central Park jogger case, for example, but campaigned for no prison time in his acquaintance Mike Tyson’s rape case.

Here’s a brief history of Trump’s statements on sexual assault, including his reaction to former Rep. Todd Akin’s infamous “legitimate rape” remark and his evolving responses to the allegations against comedian Bill Cosby.

The Central Park jogger case

Back in 1989, Trump took an intense interest in the case of five black and Hispanic youths who were accused of brutally beating and raping a young banker as she went for a run through the park. He went as far as taking out full-page ads that blared “BRING BACK THE DEATH PENALTY” across the top and touted execution as a deterrent for other potential “muggers and murderers.”

The five defendants in the case eventually had their convictions overturned in 2002, after evidence emerged that their confessions had been coerced and a serial rapist had confessed to the crime. They went on to settle with the city of New York for $40 million in 2014.

That settlement incensed Trump. He wrote an op-ed column for the New York Daily News that blasted the settlement as a “disgrace” and suggested the five men were not innocent, despite the reversal of their convictions.

“Speak to the detectives on the case and try listening to the facts,” he wrote in the op-ed. “These young men do not exactly have the pasts of angels.”

Mike Tyson

Trump campaigned for a lenient sentence for former heavyweight boxer Mike Tyson, whom he’d advised in the past, after Tyson was convicted of raping an 18-year-old girl in 1992. The real estate mogul proposed that Tyson be ordered to pay millions of dollars to his victim and into a fund for other rape survivors rather than serve a prison sentence.

“As everybody knows, I am very strong on the death penalty and for the strongest of sanctions and hardest of disciplines for anyone,” Trump said in an interview with Newsday at the time. “But far more people can be helped by allowing the tremendous sums of money from his fights to be put into funds used for rape victims.”

Tyson was ultimately sentenced to 10 years in prison, but a judge suspended four years of that sentence.

Todd Akin

Trump wasn’t a fan of the “legitimate rape” remark that cost former Rep. Todd Akin (R-MO) a U.S. Senate seat in Missouri during the 2012 election cycle. Akin said in a TV interview that “the female body has ways to try to shut” a pregnancy down if it results from “legitimate rape.” The real estate mogul acknowledged in a CNBC interview that Akin’s comment was “terrible” but said the candidate must have made a “mistake.”

“I thought it was terrible,” Trump said on CNBC’s “Squawk Box.” “I watched the statement and I thought it’s inexcusable. I assume it was horribly crafted. I can’t believe he’s there in terms of mentality to make a statement like that. So I assume he just made a mistake in the way that he said it, but maybe that’s not the case.”

Trump continued to wrestle with the notion that Akin could have actually believed what he said.

“I just don’t know, does he believe that? Is that what he really believes, what he said, or did he just say it incorrectly?” the billionaire mused. “If he said it incorrectly he’s just got to get out there and apologize in a better form than he did.”

Sexual assault in the military

Trump was heavily criticized in 2013 for his response to a report on rampant sexual abuse in the military:

26,000 unreported sexual assults in the military-only 238 convictions. What did these geniuses expect when they put men & women together?

The real estate mogul seemed to imply that rape is the inevitable result of men and women being in one another’s company. In true Trump fashion, he had a retort ready for those who read his tweets that way.

“For all of the morons who have been complaining about my comment on sexual assault & rape in the military, don’t you see that it was asked as a question, with a question mark at the end of the sentence!” he tweeted. “In other words, it wasn’t made as a statement, but rather as a question. I wanted your views. Many of the generals and military officials were not in favor of the male/female mix. What do you think of that?”

It’s important to note that the episode, which aired in January, was filmed months before accusations of sexual assault against Cosby were given renewed attention in the press and dozens of alleged victims stepped out of the shadows. Trump tweeted that despite the comedy legend’s alleged transgressions, Pulliam “still should have asked him for money-goes to charity,” and other celebrities accused the real estate mogul of capitalizing on that awkward moment for ratings.

This month, however, Trump was prepared to unequivocally call out Cosby. He told New York radio station WABC that he thought Cosby was “guilty as hell” and insisted he’s “never been a fan” of the comedian.

Mexicans immigrants are “rapists”

At the very top of his June presidential announcement speech, Trump went on a tirade against immigrants crossing the U.S. border with Mexico.

Those comments cost the billionaire several lucrative business relationships in the following weeks, from his deals with NBC and Univision to licensing Trump merchandise to Macy’s and Serta. But the presidential candidate kept repeating the “rapists” line at campaign events and in interviews.

In an interview earlier this month, CNN’s Don Lemon pressed Trump about where he got his information about rapists crossing the border. When Trump referenced articles about the rampant sexual abuse of women migrating into the U.S., Lemon pointed out that such news stories don’t also indicate criminals were entering the country.